The Girlfriends Guide to Chicago

I recently got back from a fun Weekend Girls Trip exploring Chicago with my good friend Lauren. We both live on opposite sides of the United States; I’m on the West Coast, and Lauren is on the East Coast. Unfortunately, since we don’t live close, we don’t get to hang out with each other as often as we want to (thank goodness for Google Chats!). Yup, we’re bloggers turned real-life friends! Enter the idea for a girls trip to Chicago! We loved the idea of exploring a new to us city, checking out the local food scene, sights and skyline and it quickly became a no-brainer that Chicago was the perfect spot for us meet up. Plus, we both found incredible deals on airline tickets, with us both arriving in Chicago about a half hour apart. 

Lauren flew in from Atlanta, and I flew into Chicago from Sacramento. We planned to see all the sights, eat all the food, stay caffeinated, have hours of girl talk and uncover the best spots in Chicago for an ultimate weekend girls trip. Together we’ve created the Girlfriends Guide to Chicago, a first of many! Our guide is the ultimate guide to exploring Chicago with your girlfriend, sharing our favorite coffee spots, best places for lunch, best Chicago Deep dish pizza + insider tips for saving money while visiting Chicago and more!  *This post contains sponsored content, please note all words and opinions shared are our own.  


The Girlfriends Guide to Chicago


Hilton // While in Chicago, Lauren and I stayed at the Hilton Chicago, right on Michigan Avenue.  The hotel was lovely, huge in fact. It’s the 3rd largest hotel in Chicago and historic! The Hotel was built in the 1920’s, the interior stunning and the rooms vast and modern with perfect city views. The Hilton is in a perfect location and conveniently located within walking distance to the top Chicago attractions including Grant Park, Buckingham Fountain, Millennium Park, Chicago Cultural Museum and more. *Insider Tip: Visit the Rooftop Deck on the 9th floor in the morning for a pretty Sunrise view overlooking the city.

Chicago Athletic Association Hotel // From the moment you walk into Chicago Athletic Association Hotel, the vibe inside has fun, relaxed and had a playful atmosphere. The hotel is a Venetian Gothic historical landmark built in the 1890’s as an Athletic Club and reimagined as a hotel in 2015. The inside of the hotel is just stunning and non-fussy. Inside the hotel, there’s a Shake Shack, Fairgrounds Coffee, and on the second floor there’s a Game Room that also serves amazing cocktails and good eats. The hotel also boasts a fantastic restaurant Cindy’s with an incredible rooftop deck (more on that below). 

Hotel Lincoln // If you're staying in Chicago more than three nights, it's essential to mix up your accommodations and stay in another area of Chicago. Hotel Lincoln is in the heart of the Lincoln Park neighborhood within walking distance to Old Town, The Lincoln Park Conservatory and the L. The rooms are modern with a vintage vibe thanks to the styling of Jonathan Adler with incredible room views. Inside the hotel boasts a relaxing coffee shop, restaurant and rooftop bar, The J Parker, with sweeping views of Lincoln Park and beyond (spilling more tea on that below). 


It’s amazing how many free sights a massive city like Chicago has to enjoy. We’ve rounded up our favorite free spots to visit while in Chicago. 

Grant Park, Buckingham Fountain & Millennium Park // Grant Park is stunning and encompasses over 316 acres right on the loop in Chicago.  The park is filled with gardens, tennis courts, and even baseball fields! Buckingham Fountain is so pretty and huge. In fact, it's one of the most massive fountains in the world. The fountain is directly across from Lake Michigan. A visit to Millennium Park to see Cloud Gate is a must, it's so pretty in person and so reflective! We loved snapping pictures and people watching while there. In addition, there’s also the Crown Fountain and Lurie Gardens. *Insider Tip: Ever wonder how bloggers take pics and it seems as if they’re the only ones at a huge monument? It’s simple, get there early! If you want pictures at the Cloud Gate without a ton of people in the background, get there before 9:00 am/ An obligatory selfie at the Cloud is a must!


Chicago Cultural Museum, Riverwalk // The Chicago Cultural Museum is free and open year-round to the public. It was built in the 1890’s and features a Tiffany Glass dome inside; it's stunning! When we visited, we saw the Room of Plinths Exhibition featuring mini rooms; it was so cool! One thing that I really loved about Chicago is the river that runs through the city. The Riverwalk is a walkway that contains seating areas, restaurants and more. *Insider Tip: After  visiting the Cultural Museum stop in Toni Patisserie & Cafe for lunch or dessert to go (more deets below). 

Navy Pier, Ohio Street Beach //  Navy Pier reminded me so much of San Francisco's Pier 39, a huge tourist attraction. Even though there are a bunch of tourists wandering around it's a great place to see incredible views of both Lake Michigan and the Chicago skyline, ride a Ferris wheel (personally they scare me) and eat some candied nuts, but skip the pier food and enjoy local fare instead. Sadly we didn’t have a chance to check out Ohio State Beach, but all the locals told us the beach is an excellent spot for open water swimming weather permitting! It's also a beautiful place to walk along the shoreline. 

 view from Navy Pier of the Chicago Skyline 

view from Navy Pier of the Chicago Skyline 

Lincoln Park Conservatory, Old Chicago & Neighborhood Walk // Visiting the Lincoln Park Conservatory is a must! The conservatory was built in the 1890’s and it's stunning! Inside each of the green rooms, you’ll find an incredible array of plants from all over the globe. The Conservatory is right next to the Lincoln Park Zoo, which is also free! While in Lincoln Park, visit Old Town. It's filled with various restaurants, historic buildings and local shops. Walking through neighborhoods is a must for me. I love exploring areas on foot; I adore homes and seeing how people live. The Lincoln Park neighborhoods didn’t disappoint. The streets are tree-lined and the brownstones amazing. I love how it's within walking distance to the parks, grocery stores and local pubs. The area has a great vibe. *Insider Tip: Before walking to the Conservatory, stop by Elaine’s Coffee Call inside of Hotel Lincoln for lattes. 




Goddess and the Baker // We loved Goddess and the Baker, a fun coffee shop + bakery that also serves up tasty breakfast, lunch, dinner, and desserts (and handmade gelato!). We even love their motto ‘Eat Now Caffeinate’. The vibe inside was relaxing, music fantastic and lattes amazing! I quickly fell in love with their vanilla lattes paired with delicious oatmeal, while Lauren loved the smoked salmon plate with a chai latte. Goddess and the Baker was one of our favorite spots for breakfast before starting our day exploring Chicago. 

Peach & Green // Peach & Green has good seasonal fresh food and is an excellent spot for morning breakfast. Plus they have lattes, and I love lattes! Along with the lovely ambiance inside, the staff is friendly and the food is excellent. We loved the breakfast burritos, and their waffles sounded good too. Lauren and I have a soft spot for cookies and we each got giant cookies to go. I got the peanut butter and Lauren got the chocolate chip cookie. 

Elaine’s Coffee Call // Before heading to Lincoln Park Conservatory, we stopped in Elaine’s Coffee Call, located at Hotel Lincoln. The vibe and decor inside Elaine’s is fun and the lattes strong and hot! It was perfect for chilly Fall days in Chicago. *Insider Tip: Sit on the sofa in front of the building for people watching and the pretty wallpaper inside makes for great Instagram captures. 


Stans Donuts // We were on a mission to find the best donut spot in Chicago and we did! Stan’s Donuts has incredible homemade donuts, and it's so darn cute inside! It was so Instagrammable! Yes, that’s a word! My favorite was the Lemon Pistachio Old-fashioned, it was terrific! Lauren’s loved the Strawberry bismark. We were both in donut heaven and also enjoyed their lattes! 

Duck Duck Goat // On our first day in Chicago, we went to Duck Duck Goat for Dim Sum Brunch. It was our first time having Dim Sum Brunch, so we decided to be adventurous and have the chef select our dishes! The dishes were incredible, and we both agreed next time we’re in Chicago, we’re heading back to Duck Duck Goat. Out of all the dishes, we had three favorites: Jiaozi potstickers, Beef Slap Noodles and the Duck Fried Rice. When enjoying brunch, drinks are a must! We both said cheers with Boozy Bubbles Chai Tea, yummy! I also loved the outside of the restaurant, a pretty navy exterior paired with a yellow awning. Once inside the restaurant, the interior is a feast for the eyes with each room within Duck Duck Goat feeling like its own space; so much stunning decor! *Insider Tip: Sit in the Pink Room as we called it for the best spot in the house + great views of the bar! 



Nando’s Peri Peri Chicken // We loved visiting Nando’s on Michigan Avenue for a vibrant lunch. The location just opened a few months ago. Nando’s serves up a spicy combination of South African and Portuguese food; the blend is flavorful. Inside the decor is lively and the music is so good (can they please sell the soundtrack! lol). I also loved the decor, artwork and all the pretty inside plants (hello Fiddle Leaf Fig envy!). We suggest when you visit grab all the sauces and have fun! *Insider Tip: Sit in the Patio Garden for a great view of Chicago sights.


Toni Patisserie & Cafe // As I mentioned our days were jam-packed full of places to visit, which made our visit to Toni Patisserie & Cafe extra special. We enjoyed a relaxing French-inspired lunch of crepes, lattes, and dessert. In addition to amazing crepes, the cafe has a fantastic assortment of desserts including French Macaroons. It was lovely to have a relaxing lunch place to chat about the morning adventures. Toni Patisserie is conveniently located near all the top Chicago attractions including Millennium Park and the Chicago Cultural Museum. 


My girl Lauren is taking over the post! Lauren is the owner of Color Hug; teaching bloggers & creativepreneurs to maximize their time with E-course/tips and strategies. Lauren is my go-to girl for all things blogging + good friend! Take it away L! 


Cindy’s Rooftop // Cindy’s Rooftop was the highlight of my trip to Chicago (outside of hanging with Katrina!).  I am a sucker for a view from above, so throw in the sunset on the lake, views of Millennium Park and beyond, a delicious handcrafted cocktail and a roaring firepit?? I was in heaven!  Cindy’s is located on the 13th  floor of the Chicago Athletic Association Hotel.  I had the Grey Garden (tito’s, dolin blanc, crème de violette, emperor’s jasmine pearl tea, lemon- This refreshing cocktail with a dusty lavender hue evokes a lush garden) and Katrina had the Kick in the Daisy (herradura reposado, ancho reyes, licor 43, fresh watermelon, lime, maldon sea salt. A watermelon Margarita with hints of marshmallow giving way to a lingering burn).  Both cocktails were delicious and the perfect end to a busy day.  They are also open late night; they close between 1AM-2AM depending on the day of the week. *Insider Tip: Skip visiting the Willis Tower and visit Cindy’s instead!  You get an incredible view, and the price of two mind blowing cocktails is less than two admission tickets to the SkyDeck.  Also, the weekends here are bonkers...visit on a weekday evening to cut down on the crowd.


The J. Parker // This was also a rooftop restaurant and bar that we unfortunately didn’t have time to visit.  The J. Parker is located on the 13th floor of Hotel Lincoln in the Lincoln Park neighborhood.  They get an honorable mention because of their beautiful unobstructed views of the water, their plentiful outdoor seating and their delicious cocktail menu.

 image via  Trip Adviser

image via Trip Adviser


Lou Malnati’s // As mentioned before, this was our first trip to Chicago, so it was pertinent to try out a Chicago style deep dish pizza!  We visited Lou Malnati’s flagship location in Gold Coast and had the best deep dish pizza we have ever tried!  To start, the interior was gorgeous.  The dining areas in the front of the restaurant included brown leather couches, plenty of glass windows and gorgeous light fixtures with Edison light bulbs.  As you walk through the restaurant, you see plenty of high top tables and chairs in turquoise and brown, and the lighting is dim which gives it a perfect nighttime vibe.  The appetizers were great (pizza chips with three types of dip...I’ve never even heard of pizza chips!), and the deep dish was amazing!  We had the Malnati Chicago Classic and the “Lou”.  Both were awesome, but what I loved most about the Classic was that the sausage was lean, so the pizza was not oily at all!  Also, I loved both deep dishes because I’m not a pizza crust fan, so the toppings went all the way to the edge of the crust (Yaaassss!!!). *Insider Tip: If you love sports, be sure to get a seat in the bar area so that you can watch the game on their big screen.  If you’d rather people watch outside, try to sit in the front of the restaurant. One last tip, you can also Ship a Pizza and bake it at home, so doing this for Christmas Eve! 


Tuco and Blondie // We didn’t get a chance to make it to Tuco and Blondie, but they get an honorable mention!  This is a Tex-Mex restaurant that has the most vibrant interior and they get bonus points for having a colorful exterior wall perfect for Instagram shots (I know I’m not the only one who rates a place based on their Instagramability, lol!).  They also have a mouthwatering menu and their cocktails look and sound amazing!  This is a place that we will definitely visit on our next trip to Chicago.

 image via  DNA Info

image via DNA Info


Nutella Cafe // This place gets an honorable mention!  Though we didn’t get a chance to try them out, every time we walked past it there was a line OUT THE DOOR! There was even an employee that was handing out menus to people in line.  This is a small cafe, but since it is the first of it’s kind in the U.S., it’s still wildly popular (they opened in May 2017).  They are open until 9pm-10pm depending on the day that you visit, so this is a perfect place to grab a bite and a sweet treat at night.

 image via  Eater Chicago

image via Eater Chicago

Portillo’s // Since this was our first visit to Chicago, it was crucial to try a Chicago style hot dog!  I was personally geeked about this because I love hot dogs, so visiting Portillo’s was a treat.  We went to the Clark and Ontario location which has a 30’s, 40’s gangster theme inside and was HUGE!  There are five different sections where you can order different types of cuisine.  Along with the delicious Chicago style hot dogs, they also serve burgers, ribs, Italian beef sandwiches, specialty salads, pasta, and desserts such as their famous chocolate cake (delicious!), chocolate cake shake, eclairs and more!  This is a perfect place to visit not only for lunch or dinner, but if you have a late night craving because they are open until 11pm-12pm depending on the day of the week. *Insider Tip: A Chicago dog includes mustard, onions, relish, tomatoes, a pickle spear and sport peppers on a steamed poppyseed bun.  It might sound like too much, but just order the dog Chicago style even if you’re unsure about it!  Also, for a hot dog place, their italian meatball with garlic bread was phenomenal!



Chicago Transit Authority (AKA CTA) // We started our trip taking the “L” from the airport into the city.  It’s always great to take a train from the airport depending on how far it is from where you’re staying.  It was around a 45 minute train ride to the city, so we were able to see various parts of Chicago and the surrounding areas along the way. We purchased a three day pass which gave us unlimited access to the CTA trains and buses. It was a steal at $20 a ticket. The train and bus systems were fairly easy to understand, so we were able to visit areas that were a little farther away from the city center as a result.


Lyft + Uber // Lyft and Uber were our besties during this trip! We mostly took them at night when we were headed to and from dinner because we didn’t want to deal with public transportation too late at night.  We even saved some coins by doing ride shares meaning that it was a possibility that we would be sharing the same car with someone else that was headed in the same direction.  We were cool with this saved coins!  If you have never used Lyft or Uber, you can sign up with our codes to get credits on your first rides. Sign up for Uber here and sign up for Lyft here*Insider Tip: Don’t be afraid to combine your modes of transportation because it may be more economical and save time.  For example, we took an Uber to the train station when we headed back to the airport.  It was cheaper and faster to Uber to the station than to walk to the station or Uber all the way to the airport!  Plus, when you take the train, highway traffic is no longer an issue.

Walkable Chicago // Walking was our number one way of getting around Chicago.  The city is incredibly walkable and you don’t even realize how much you have walked because there is so much to see around every corner.  We walked 7 miles on Sunday and 8 miles on Monday which was awesome because we didn’t feel so bad about indulging in sweets, lattes and the like :) Just be sure to wear comfortable walking shoes because sore feet are no fun!
*Insider Tip: Comfortable walking shoes can be cute, too!  Check out this cute leopard pair that Katrina wore.


Google Maps // Absolutely none of our movement would have been possible without Google Maps.  Katrina planned out a walking map for each day of our trip, and if we decided to change something up, we just went to the app and found out how to get there whether we were walking or using CTA.  It even told us what bus and train to get on and how far away they were from us in real time!  Lastly, I was surprised to see that you can even use Lyft and Uber through the Google Maps app!


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We covered so much ground while in Chicago for three nights and four days + the first day when we arrived it poured! Thankfully the sunny skies came out and we had an absolute blast! I seriously loved Chicago and can't wait to return. Girls trips are the best! In fact, we have our next three cities lined up and ready to explore together. Lauren and I know this was a crazy long post, but we're hoping you loved all The Tea we spilled.

Tell us, when was your last girls trip and where did you go? Also, have you visited Chicago before? If so, what was your best memory of the city? Lastly, where are you heading for your next trip?